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Introducing an In Situ Capping Strategy in Systems Biocatalysis To Access 6-Aminohexanoic acid
- Source :
- Angewandte Chemie International Edition. 53:14153-14157
- Publication Year :
- 2014
- Publisher :
- Wiley, 2014.
-
Abstract
- The combination of two cofactor self-sufficient biocatalytic cascade modules allowed the successful transformation of cyclohexanol into the nylon-6 monomer 6-aminohexanoic acid at the expense of only oxygen and ammonia. A hitherto unprecedented carboxylic acid capping strategy was introduced to minimize the formation of the dead-end intermediate 6-hydroxyhexanoic acid. For this purpose, the precursor e-caprolactone was converted in aqueous medium in the presence of methanol into the corresponding methyl ester instead of the acid. Hence, it was shown for the first time that esterases--specifically horse liver esterase--can perform the selective ring-opening of e-caprolactone with a clear preference for methanol over water as the nucleophile.
- Subjects :
- chemistry.chemical_classification
Molecular Structure
Chemistry
Carboxylic acid
Cyclohexanol
Esterases
General Medicine
General Chemistry
Cyclohexanols
Catalysis
Enzyme catalysis
chemistry.chemical_compound
Ammonia
Monomer
Nucleophile
Liver
Biocatalysis
Aminocaproic Acid
Organic chemistry
Animals
Methanol
Horses
Subjects
Details
- ISSN :
- 14337851
- Volume :
- 53
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....9f5f622e1e27443ff026d8ee5d1813d3